Synthesis of a Phlorin from a Meso‐Fused Anthriporphyrin by a Diels–Alder Strategy

Abstract

AbstractAn anthracene‐containing meso‐fused carbaporphyrin, which has extended π‐conjugation pathways as compared to the corresponding naphthalene‐containing carbaporphyrin, has been synthesized. The weak global aromaticity of the anthriporphyrin also allowed its use as the diene for a Diels–Alder reaction with dimethyl acetylenedicarboxylate (DMAD). The resulting phlorin contains an interesting bicyclic structure. Moreover, to the best of our knowledge, this phlorin is the first Diels–Alder adduct of a diene forming part of the global π‐conjugation pathway of an aromatic porphyrinoid.